Composition comprising a pesticide and an alkoxylate of 2-propylheptylamine

ABSTRACT

The present invention relates to a composition comprising a pesticide and an alkoxylate. Moreover, the invention relates to the alkoxylate, to a process for its preparation and to its use as adjuvant in pesticide-comprising spray mixtures. The invention furthermore relates to a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesirable plants and/or the crop plants and/or their environment. Furthermore, the invention relates to seed comprising the composition.

This application is a Continuation of U.S. application Ser. No.13/007,187, filed Jan. 14, 2011, which claims the benefit of U.S.Provisional Application No. 61/295,784, filed Jan. 18, 2010, the entirecontents of which are hereby incorporated herein by reference. Thisapplication also claims priority under 35 U.S.C. §119 to European PatentApplication No. 10157267.5 filed Mar. 23, 2010, the entire contents ofwhich is hereby incorporated herein by reference.

The present invention relates to a composition comprising a pesticideand an alkoxylate. Moreover, the invention relates to the alkoxylate, toa process for its preparation and to its use as adjuvant inpesticide-comprising spray mixtures. The invention furthermore relatesto a method of controlling phytopathogenic fungi and/or undesiredvegetation and/or undesired insect or mite attack and/or for regulatingthe growth of plants, wherein the composition is allowed to act on therespective pests, their environment or the plants to be protected fromthe respective pest, on the soil and/or on undesirable plants and/or thecrop plants and/or their environment. Furthermore, the invention relatesto seed comprising the composition. The present invention comprisescombinations of preferred features with other preferred features.

Alkoxylates and their use in agrochemical formulations as adjuvants aregenerally known:

WO 2009/004044 discloses a herbicidal composition comprising aphenoxy-acid herbicide and an alkoxylated alkylamine as adjuvant, itbeing possible for the alkylamine, for example, to be a2-propylheptylmethylamine which is alkoxylated with 3 to 20 ethyleneoxide groups.

U.S. Pat. No. 5,668,085 discloses a herbicidal composition comprising anaqueous solution of glyphosate and surfactant. The surfactant may be analkoxylated alkylamine, the alkyl group comprising 8 to 22 carbon atoms.

Alkoxylated alkylamines, in particular commercially availableethoxylated tallow fatty amines (POEA), have important toxic properties(such as irritation of the skin and the eyes) and ecotoxic properties(such as high ecotoxicity to aquatic organisms such as algae anddaphnias). Thus, for example, POEA (CAS No. 61791-26-2), which isfrequently present in Roundup® herbicides as a wetter, is considered tobe relatively toxic to aquatic organisms (Tsui and Chu, Chemosphere2003, 52, 1189-1197).

It was therefore an object of the present invention to find an adjuvantwhich is well suited to herbicides such as glyphosate while being lesstoxic (especially lower toxicity to aquatic organisms). Furthermore, theadjuvant should make possible a storage-stable formulation of thepesticides.

The object was solved by a composition comprising a pesticide and analkoxylate, wherein the alkoxylate is an amine alkoxylate (A)

or a quaternized derivative (AQ)

of the amine alkoxylate (A), where

-   R¹, R², and R⁵ independently of one another are ethylene, propylene,    butylene or a mixture of these,    -   R³ is an H, —OH, —OR⁴, —[R⁵—O]_(p)—R⁶, C₁-C₆-alkyl or an oxygen        anion,-   R⁴ is a C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl,-   R⁶ is an H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —SO₃R^(a),    —P(O)OR^(b)OR^(c), —CH₂CO₂R^(d), or —C(O)R^(e),-   R^(a) and R^(d) independently of one another are an H, inorganic or    organic cations,-   R^(b) and R^(c) independently of one another are an H, inorganic or    organic cations, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl,-   R^(e) is C₁-C₂₂-alkyl, C₂-C₂₂-alkenyl, C₂-C₂₂-alkynyl, C₆-C₂₂-aryl    or C₇-C₂₂-alkylaryl, n, m and p independently of one another have a    value of from 1 to 30,-   A⁻ is an agriculturally acceptable anion, or, if R³ is an oxygen    anion, A⁻ is absent.

Preferably, the composition according to the invention comprises apesticide and an alkoxylate, wherein the alkoxylate is an aminealkoxylate (A).

Preferably, n has a value of from 1 to 20, especially preferably from 1to 15. Preferably, m has a value of from 1 to 20, especially preferablyfrom 1 to 15. Preferably, p has a value of from 1 to 30, especiallypreferably from 1 to 20. The values of n, m and o are normally averagevalues as they mostly arise upon the alkoxylation with alkoxides.

Therefore, n, m and o can not only be integers, but also all valuesbetween the integers.

Preferably, in the case of the amine alkoxylate (A), the total of n andm is 2 to 40 and in its quaternized derivative (AQ) the total of n, mand p is 3 to 80.

In the case of the amine alkoxylate (A) the total of n and m isespecially preferably 3 to 30 and specifically 5 to 25. In a furtherespecially preferred embodiment, the total of n and m is 6 to 9, inparticular 6.5 to 8.5 and in particular 6.9 to 7.9. In a furtherespecially preferred embodiment, the total of n and m is 11 to 40, inparticular 12 to 30 and in particular 13.5 to 25. In a furtherespecially preferred embodiment, the sum of n and m is 8 to 13, inparticular 9 to 11.

In the case of the quaternized derivative (AQ) of the amine alkoxylate(A), the total of n, m and p is especially preferably 3 to 40 andspecifically 5 to 25. In one especially preferred embodiment, the sum ofn and m is 8 to 13, in particular 9 to 11.

R¹, R² and R⁵ are preferably independently of one another ethylene,ethylene and propylene, ethylene and butylene, or ethylene, propyleneand butylene. In a further preferred embodiment, R¹, R² and R⁵ arepropylene. In a further preferred embodiment, R¹, R² and R⁵ arebutylene. Especially preferably R¹, R² and R⁵ independently of oneanother are ethylene, or ethylene and propylene. Very especiallypreferably, R¹, R² and R⁵ are ethylene.

If R¹, R² or R⁵ comprise a butylene radical, the latter may be presentas a n-butylene, an isobutylene or a 2,3-butylene group, with n-butyleneand isobutylene being preferred and n-butylene being most preferred.

R¹, R² and R⁵ independently of one another may be a mixture of ethylene,propylene or butylene. In this context, for example one or all radicalsR¹, R² and R⁵ may comprise a mixture of these groups in each alkoxylatechain. Such mixtures can be linked to one another in any desired order,for example randomly or blockwise (such as one block ethylene and oneblock propylene). Also, it is possible for in each case one or more ofthe radicals R¹, R², and R⁵ to form a complete alkoxylate chain composedof different alkylene groups. For example, R¹ and R² may be composed ofethylene and R⁵ of propylene.

R³ is preferably an H, —OH, C₁-C₄-alkyl or an oxygen anion, it isespecially preferably an H, methyl, butyl or an oxygen anion. In aspecifically preferred embodiment, R³ is a methyl. In a furtherspecifically preferred embodiment, R³ is an oxygen anion. In a furtherspecifically preferred embodiment, R³ is an H.

R⁴ is preferably a C₁-C₆-alkyl, in particular a methyl or butyl,especially butyl.

R⁶ is preferably an H or C₁-C₆-alkyl, more preferably an H or methyl,especially H.

R^(a) and R^(d) are independently of one another H, or inorganic ororganic cations, which may be singly or multiply positively charged.Examples of inorganic cations are cations of ammonium, Na⁺, K⁺, Mg²⁺,Ca²⁺, or Zn²⁺. Examples of organic cations are methyl-ammonium,dimethylammonium, trimethylammonium, tetramethylammonium,(2-hydroxyethyl)ammonium, bis(2-hydroxyethyl)ammonium,tris(2-hydroxyethyl)-ammonium, tetra(2-hydroxyethyl)ammonium.Preferably, R^(a) and R^(d) independently of one another are H orinorganic cations. If an inorganic or organic cation is present, thenthe associated anionic group would be formed by the correspondingfunctional group (e.g., —SO₃ ⁻, —P(O)O⁻O⁻, or —CH₂CO₂ ⁻) on R⁶.

R^(b) and R^(c) are preferably, independently of one another, H,inorganic or organic cations. Suitable inorganic or organic cations arethose specified under R^(a).

In another embodiment, in the quaternary derivative (AQ), the radicalsR^(a), R^(b), R^(c) and R^(d) independently of one another may beorganic cations, with the cationic group being the quaternary nitrogencation of AQ itself. It would also be possible, therefore, for AQ toform a zwitterion, with the anionic group being formed by thecorresponding functional group (e.g., —SO₃ ⁻, —P(O)O⁻O⁻, or —CH₂CO₂ ⁻)on R⁶ in AQ, and the cationic group by the quaternary nitrogen of AQ. Inthis zwitterionic form of AQ, the presence of an agriculturallyacceptable anion A⁻ is optional.

R^(e) is preferably C₁-C₁₂-alkyl, C₆-C₁₂-aryl, or C₇-C₁₂-alkylaryl, morepreferably C₁-C₆-alkyl.

A⁻ is an agriculturally acceptable anion, as they are generally known tothe skilled worker. Preferably, A⁻ is a halide (such as chloride orbromide), phosphate, sulfate or an anionic pesticide. Especiallypreferably, A⁻ is an anionic pesticide, such as a glyphosate anion orglufosinate anion. If R³ is an oxygen anion, an amine oxide is present.In this case, a further anion such as A⁻ is absent.

In the case of the amine alkoxylate (A), it is preferred that R¹ and R²independently of one another are ethylene, ethylene and propylene,ethylene and butylene, or ethylene, propylene and butylene, and thetotal of n and m is 2 to 60, preferably 2 to 40, especially preferably 3to 30 and in particular 5 to 25. In a further preferred embodiment, R¹and R² are ethylene, ethylene and propylene, ethylene and butylene, orethylene, propylene and butylene and the total of n and m is 6 to 9, inparticular 6.5 to 8.5 and in particular 6.9 to 7.9 In a furtherpreferred embodiment, R¹ and R² are ethylene, ethylene and propylene,ethylene and butylene, or ethylene, propylene and butylene and the totalof n and m is 11 to 40, in particular 12 to 30 and in particular 13.5 to25. In one particularly preferred embodiment, R¹ and R² are ethylene,ethylene and propylene, ethylene and butylene, or ethylene, propyleneand butylene, and the sum of n and m is 6 to 14, more particularly 8 to12, and especially 9 to 11.

In the case of the amine alkoxylate (A), it is especially preferred thatR¹ and R² are ethylene, and the total of n and m is 2 to 60, preferably2 to 40, especially preferably 3 to 30, and in particular 5 to 25. In afurther especially preferred embodiment, R¹ and R² are ethylene and thetotal of n and m is 6 to 9, in particular 6.5 to 8.5 and in particular6.9 to 7.9. In a further especially preferred embodiment, R¹ and R² areethylene and the total of n and m is 11 to 40, in particular 12 to 30and in particular 13.5 to 25.

The compounds (A) and (AQ) may be present as mixtures of stereoisomersor as isolated stereoisomers. Tautomers and betaines are likewiseencompassed by the structures (A) and (AQ).

In most cases, the composition according to the invention comprises from0.1 to 90% by weight of the alkoxylate, preferably from 1 to 50% byweight and in particular from 3 to 30% by weight.

The term pesticide refers to at least one active substance selected fromthe group of the fungicides, insecticides, nematicides, herbicides,safeners, molluscicides, rodenticides and/or growth regulators.Preferred pesticides are fungicides, insecticides, herbicides and growthregulators. Especially preferred pesticides are herbicides and growthregulators. Mixtures of pesticides from two or more of theabovementioned classes may also be used. The skilled worker is familiarwith such pesticides, which can be found, for example, in PesticideManual, 14th Ed. (2006), The British Crop Protection Council, London.Suitable pesticides are:

A) Strobilurins:

-   azoxystrobin, dimoxystrobin, coumoxystrobin, coumethoxystrobin,    enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin,    orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin,    pyraoxystrobin, pyribencarb, trifloxystrobin, methyl    2-[2-(2,5-dimethylphenyloxymethyl)phenyl]-3-methoxyacrylate,    2-(2-(3-(2,6-di-chlorophenyl)-1-methylallylideneaminooxymethyl)phenyl)-2-methoxyimino-N-methylacetamide;

B) Carboxamides:

-   -   carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen,        boscalid, carboxin, fenfuram, fenhexamid, flutolanil,        furametpyr, isopyrazam, isotianil, kiralaxyl, mepronil,        metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl,        oxycarboxin, penflufen        (N-(2-(1,3-dimethylbutyl)phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide),        penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil,        2-amino-4-methylthiazole-5-carboxanilide,        N-(3′,4′,5′-trifluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,        N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,        N-(2-(1,3,3-trimethylbutyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide;    -   carboxylic acid morpholides: dimethomorph, flumorph, pyrimorph;    -   benzamides: flumetover, fluopicolide, fluopyram, zoxamid;    -   other carboxamides: carpropamid, diclocymet, mandipropamid,        oxytetracyclin, silthiofam,        N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide;

C) Azoles:

-   -   triazoles: azaconazole, bitertanol, bromuconazole,        cyproconazole, difenoconazole, diniconazole, diniconazole-M,        epoxiconazole, fenbuconazole, fluquinconazole, flusilazole,        flutriafol, hexaconazole, imibenconazole, ipconazole,        metconazole, myclobutanil, oxpoconazole, paclobutrazole,        penconazole, propiconazole, prothioconazole, simeconazole,        tebuconazole, tetraconazole, triadimefon, triadimenol,        triticonazole, uniconazole;    -   imidazoles: cyazofamid, imazalil, imazalil sulfate, pefurazoate,        prochloraz, triflumizole;    -   benzimidazoles: benomyl, carbendazim, fuberidazole,        thiabendazole;    -   others: ethaboxam, etridiazole, hymexazole,        2-(4-chlorophenyl)-N-[4-(3,4-dimethoxy-phenyl)isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;

D) Nitrogenous Heterocyclyl Compounds

-   -   pyridines: fluazinam, pyrifenox,        3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]-pyridine,        3-[5-(4-methylphenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine;    -   pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol,        ferimzone, mepanipyrim, nitrapyrin, nuarimol, pyrimethanil;    -   piperazines: triforine;    -   pyrroles: fludioxonil, fenpiclonil;    -   morpholines: aldimorph, dodemorph, dodemorph acetate,        fenpropimorph, tridemorph;    -   piperidines: fenpropidin;    -   dicarboximides: fluorimid, iprodione, procymidone, vinclozolin;

nonaromatic 5-membered heterocyclic rings: famoxadon, fenamidon,flutianil, octhilinone, probenazole, S-allyl5-amino-2-isopropyl-3-oxo-4-orthotolyl-2,3-dihydro-pyrazole-1-thiocarboxylate;

-   -   others: acibenzolar-5-methyl, amisulbrom, anilazin,        blasticidin-S, captafol, captan, quinomethionate, dazomet,        debacarb, diclomezine, difenzoquat, difenzoquat methylsulfate,        fenoxanil, folpet, oxolinic acid, piperalin, proquinazid,        pyroquilon, quinoxyfen, triazoxide, tricyclazole,        2-butoxy-6-iodo-3-propylchromen-4-one,        5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole,        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine,        5-ethyl-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ylamine;

E) Carbamates and Dithiocarbamates

-   -   thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,        methasulphocarb, metiram, propineb, thiram, zineb, ziram;    -   carbamates: diethofencarb, benthiavalicarb, iprovalicarb,        propamocarb, propamocarb hydrochloride, valiphenal,        (4-fluorophenyl)        N-(1-(1-(4-cyanophenyl)ethanesulfonyl)-but-2-yl)carbamate;

F) Other Fungicides

-   -   guanidines: dodine, dodine free base, guazatine, guazatine        acetate, iminoctadine, iminoctadine triacetate, iminoctadine        tris(albesilate);    -   antibiotics: kasugamycin, kasugamycin hydrochloride hydrate,        polyoxins, streptomycin, validamycin A;    -   nitrophenyl derivatives: binapacryl, dicloran, dinobuton,        dinocap, nitrothal-isopropyl, tecnazene;    -   organometallic compounds: fentin salts such as, for example,        fentin acetate, fentin chloride, fentin hydroxide;    -   sulfurous heterocyclyl compounds: dithianon, isoprothiolane;    -   organophosphorus compounds: edifenphos, fosetyl,        fosetyl-aluminum, iprobenfos, phosphorous acid and its salts,        pyrazophos, tolclofos-methyl;    -   organochlorine compounds: chlorthalonil, dichlofluanid,        dichlorphen, flusulfamide, hexachlorobenzene, pencycuron,        pentachlorophenol and its salts, phthalide, quintozene,        thiophanate-methyl, tolylfluanid,        N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide;    -   inorganic active substances: phosphorous acid and its salts,        Bordeaux mixture, copper salts such as, for example, copper        acetate, copper hydroxide, copper oxychloride, basic copper        sulfate, sulfur;    -   biological products for controlling fungi, plant strengthening        products: Bacillus subtilis strain NRRL No. B-21661 (for example        the products RHAPSODY®, SERENADE® MAX and SERENADE® ASO from        AgraQuest, Inc., USA.), Bacillus pumilus strain NRRL No. B-30087        (for example SONATA® and BALLAD® Plus from AgraQuest, Inc.,        USA), Ulocladium oudemansii(for example BOTRY-ZEN from BotriZen        Ltd., New Zealand), chitosan (for example ARMOUR-ZEN from        BotriZen Ltd., New Zealand).    -   others: biphenyl, bronopol, cyflufenamid, cymoxanil,        diphenylamine, metrafenon, mildiomycin, oxine-copper,        prohexadione-calcium, spiroxamin, tolylfluanid,        N-(cyclo-propylmethoxyimino-(6-difluoromethoxy-2,3-difluorophenyl)methyl)-2-phenyl-acetamide,        N′-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine,        N′-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine,        N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)phenyl)-N-ethyl-N-methylformamidine,        N′-(5-difluoromethyl-2-methyl-4-(3-tri-methylsilanylpropoxy)phenyl)-N-ethyl-N-methylformamidine,        N-methyl-(1,2,3,4-tetrahydronaphthalen-1-yl)-2-{1-[2-(5-methyl-3-trifluoromethylpyrazol-1-yl)acetyl]piperidin-4-yl}thiazole-4-carboxylate,        N-methyl-(R)-1,2,3,4-tetrahydronaphthalen-1-yl        2-{1-[2-(5-methyl-3-trifluoromethylpyrazol-1-yl)acetyl]piperidin-4-yl}thiazole-4-carboxylate,        6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate,        6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-yl methoxyacetate,        N-methyl-2-{1-[2-(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)acetyl]piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide;

G) Growth Regulators

abscisic acid, amidochlor, ancymidole, 6-benzylaminopurine,brassinolide, butralin, chlormequat (chlormequat chloride), cholinechloride, cyclanilid, daminozide, dikegulac, dimethipin,2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet,forchlorfenuron, gibberellic acid, inabenfid, indole-3-acetic acid,maleic hydrazide, mefluidid, mepiquat (mepiquat chloride), metconazole,naphthaleneacetic acid, N-6-benzyladenine, paclobutrazole, prohexadione(prohexadione-calcium), prohydrojasmone, thidiazuron, triapenthenol,tributylphosphorotrithioate, 2,3,5-triiodo-benzoic acid,trinexapac-ethyl and uniconazole;

H) Herbicides

-   -   acetamide: acetochlor, alachlor, butachlor, dimethachlor,        dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor,        napropamid, naproanilid, pethoxamid, pretilachlor, propachlor,        thenylchlor;    -   amino acid analogs: bilanafos, glyphosate, glufosinate,        sulfosate;    -   aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl,        fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop,        quizalofop, quizalofop-P-tefuryl;    -   bipyridyls: diquat, paraquat;    -   carbamates and thiocarbamates: asulam, butylate, carbetamide,        desmedipham, dimepiperat, eptam (EPTC), esprocarb, molinate,        orbencarb, phenmedipham, prosulfocarb, pyributicarb,        thiobencarb, triallate;    -   cyclohexanediones: butroxydim, clethodim, cycloxydim,        profoxydim, sethoxydim, tepraloxydim, tralkoxydim;    -   dinitroanilines: benfluralin, ethalfluralin, oryzalin,        pendimethalin, prodiamine, trifluralin;    -   diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop,        ethoxyfen, fomesafen, lactofen, oyfluorfen;    -   hydroxybenzonitriles: bromoxynil, dichiobenil, ioxynil;    -   imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr,        imazaquin, imazethapyr;    -   phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid        (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB,        mecoprop;    -   pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet,        norflurazon, pyridate;    -   pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr,        fluridone, fluoroxypyr, picloram, picolinafen, thiazopyr;    -   sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron,        chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron,        ethoxysulfuron, flazasulfuron, fluceto-sulfuron, flupyrsulfuron,        foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron,        mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron,        primisulfuron, pro-sulfuron, pyrazosulfuron, rimsulfuron,        sulfometuron, sulfosulfuron, thifensulfuron, tria-sulfuron,        tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron,        1-((2-chloro-6-propyl-imidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea;    -   triazines: ametryne, atrazine, cyanazine, dimethametryne,        ethiozine, hexazinone, metamitron, metribuzine, prometryne,        simazine, terbuthylazine, terbutryne, triaziflam;    -   ureas: chlortoluron, daimuron, diuron, fluometuron, isoproturon,        linuron, methabenzthiazuron, tebuthiuron;    -   other acetolactate synthase inhibitors: bispyribac-sodium,        cloransulam-methyl, diclosulam, florasulam, flucarbazone,        flumetsulam, metosulam, orthosulfamuron, penoxsulam,        propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalide,        pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfon,        pyroxsulam;    -   others: amicarbazone, aminotriazole, anilofos, beflubutamid,        benazolin, bencarbazone, benfluresate, benzofenap, bentazone,        benzobicyclon, bromacil, bromobutide, butafenacil, butamifos,        cafenstrole, carfentrazone, cinidon-ethlyl, chlorthal,        cinmethylin, clomazone, cumyluron, cyprosulfamid, dicamba,        difenzoquat, diflufenzopyr, Drechslera monoceras, endothal,        ethofumesate, etobenzanid, fentrazamide, flumiclorac-pentyl,        flumioxazin, flupoxam, fluorochloridon, flurtamon, indanofan,        isoxaben, isoxaflutol, lenacil, propanil, propyzamide,        quinclorac, quinmerac, mesotrione, methylarsenic acid, naptalam,        oxadiargyl, oxadiazone, oxaziclomefon, pentoxazone, pinoxaden,        pyraclonil, pyraflufen-ethyl, pyrasulfotol, pyrazoxyfen,        pyrazolynate, quinoclamin, saflufenacil, sulcotrione,        sulfentrazone, terbacil, tefuryltrione, tembotrione,        thiencarbazone, topramezone,        4-hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridin-3-carbonyl]bicyclo[3.2.1]oct-3-en-2-one,        ethyl        (3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)phenoxy]pyridin-2-yloxy)acetate,        methyl 6-amino-5-chloro-2-cyclo-propylpyrimidine-4-carboxylate,        6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-pyridazin-4-ol,        4-amino-3-chloro-6-(4-chlorophenyl)-5-fluoropyridin-2-carboxylic        acid, methyl        4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridin-2-carboxylate        and methyl        4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2-fluorophenyl)pyridin-2-carboxylate;

I) Insecticides

-   -   organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl,        chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon,        dichlorvos, dicrotophos, dimethoat, disulfoton, ethion,        fenitrothion, fenthion, isoxathion, malathion, methamidophos,        methidathion, methyl-parathion, mevinphos, monocrotophos,        oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone,        phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl,        profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos,        triazophos, trichlorfon;    -   carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb,        carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb,        methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb,        triazamate;    -   pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin,        cyphenothrin, cypermethrin, alpha-cypermethrin,        beta-cypermethrin, zeta-cypermethrin, deltamethrin,        esfenvalerate, etofenprox, fenpropathrin, fenvalerate,        imiprothrin, lambda-cyhalothrin, permethrin, prallethrin,        pyrethrin I and II, resmethrin, silafluofen, taufluvalinate,        tefluthrin, tetramethrin, tralomethrin, transfluthrin,        profluthrin, dimefluthrin,    -   insect growth inhibitors: a) chitin synthesis inhibitors:        benzoylureas: chlorfluazuron, cyramazin, diflubenzuron,        flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,        teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox,        etoxazole, clofentazin; b) ecdysone antagonists: halofenozide,        methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids:        pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis        inhibitors: spirodiclofen, spiromesifen, spirotetramate;    -   nicotine receptor agonists/antagonists: clothianidin,        dinotefuran, imidacloprid, thiamethoxam, nitenpyram,        acetamiprid, thiacloprid,        1-(2-chlorothiazol-5-ylmethyl)-2-nitrimino-3,5-dimethyl-[1,3,5]triazinane;    -   GABA antagonists: endosulfan, ethiprole, fipronil, vaniliprole,        pyrafluprole, pyriprole,        N-5-amino-1-(2,6-dichloro-4-methylphenyl)-4-sulfinamoyl-1H-pyrazole-3-thiocarboxamide;    -   macrocyclic lactones: abamectin, emamectin, milbemectin,        lepimectin, spinosad, spinetoram;    -   mitochondrial electron transport chain inhibitor (METI) I        acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad,        flufenerim;    -   METI II and III substances: acequinocyl, fluacyprim,        hydramethylnone;    -   decouplers: chlorfenapyr;    -   inhibitors of oxidative phosphorylation: cyhexatin,        diafenthiuron, fenbutatin oxide, propargite;    -   insect ecdysis inhibitors: cryomazin;    -   ‘mixed function oxidase’ inhibitors: piperonyl butoxide;    -   sodium channel blockers: indoxacarb, metaflumizon;    -   others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl,        pymetrozin, sulfur, thiocyclam, flubendiamid,        chlorantraniliprole, cyazypyr (HGW86); cyenopyrafen,        flupyrazofos, cyflumetofen, amidoflumet, imicyafos,        bistrifluoron and pyrifluquinazone.

Preferred pesticides comprise at least one pesticide with at least oneH-acidic group (such as carboxylic acid group, phosphonic acid group,phosphinic acid group) or the anionic salts thereof (e.g., mono, di ortri salts). These anionic salts of the pesticides with an H-acidic groupare also suitable as anionic pesticides in group A⁻. Preferredpesticides with an H-acidic group are herbicides with an H-acidic group.Examples of herbicides with an H-acidic group are amino acid analogs(such as glyphosate or glufosinate) or imidazolinones (such asimazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr).

Particularly preferred pesticides with an H-acidic group are glyphosateand glufosinate. In another preferred embodiment, pesticides with anH-acidic group are imidazolinones.

Especially preferably, the pesticide comprises a pesticide with anH-acidic group and a further pesticide. In another embodiment thepesticide comprises mixtures of at least two pesticides with an H-acidicgroup, and optionally further pesticides (such as at least onefungicide, herbicide, insecticide, and/or safener, with fungicidesand/or herbicides being preferred).

In a further preferred embodiment, the pesticide comprises glyphosate(for example as the free acid, sodium salt, sesquisodium salt, potassiumsalt, dipotassium salt, ammonium salt, diammonium salt, dimethylammoniumsalt, trimesium salt or isopropyl-amine sale) or glufosinate (forexample as the ammonium salt). With particular preference the pesticidecomprises glyphosate (for example as the potassium salt, ammonium saltor isopropylamine salt). With particular preference the pesticidecomprises glyphosate or glufosinate, and additionally a furtherherbicide. In another preferred embodiment the pesticide comprisesglyphosate or glufosinate, and additionally a further pesticide (such asat least one fungicide, herbicide, insecticide and/or safener, withfungicides and/or herbicides being preferred).

The compositions according to the invention can furthermore alsocomprise adjuvants conventionally used for agrochemical formulations,the choice of the adjuvants depending on the specific use form, the typeof formulation or the active substance. Examples of suitable adjuvantsare solvents, solid carriers, surface-active substances (such assurfactants, solubilizers, protective colloids, wetters and tackifiers),organic and inorganic thickeners, bactericides, antifreeze agents,antifoams, optionally colorants and adhesives (for example for thetreatment of seed) or conventional adjuvants for bait formulations (forexample attractants, feedants, bittering substances).

Suitable solvents are water or organic solvents such as mineral oilfractions of medium to high boiling point such as kerosene and dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, for example paraffins,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, glycols, ketones such ascyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fattyacids and fatty acid esters, and strongly polar solvents, for exampleamines such as N-methylpyrrolidone. In principle, it is also possible touse solvent mixtures and mixtures of the abovementioned solvents andwater.

Solid carriers are mineral earths such as silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesiumoxide, ground synthetic materials, fertilizers such as ammonium sulfate,ammonium phosphate, ammonium nitrate, ureas and vegetable products suchas cereal meal, tree bark meal, wood meal and nutshell meal, cellulosepowders or other solid carriers.

Surface-active substances (adjuvants, wetters, tackifiers, dispersantsor emulsifiers) which are suitable are the alkali metal, alkaline-earthmetal, ammonium salts of aromatic sulfonic acids, for example oflignosulfonic acid (Borresperse® types, Borregaard, Norway),phenolsulfonic acid, naphthalenesulfonic acid (Morwet® types, AkzoNobel, USA) and dibutylnaphthalenesulfonic acid (Nekal® types, BASF,Germany), and of fatty acids, alkyl- and alkylarylsulfonates, alkylether, lauryl ether and fatty alcohol sulfates, and salts of sulfatedhexa-, hepta- and octadecanols and of fatty alcohol glycol ethers,condensates of sulfonated naphthalene and its derivatives withformaldehyde, condensates of naphthalene or of the naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycolethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkylethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite liquors and proteins, denatured proteins, polysaccharides(for example methylcellulose), hydrophobe-modified starches, polyvinylalcohol (Mowiol® types, Clariant, Switzerland), polycarboxylates(Sokalan® types, BASF, Germany), polyalkoxylates, polyvinylamine(Lupamin® types, BASF, Germany), polyethyleneimine (Lupasol® types,BASF, Germany), polyvinylpyrrolidone and their copolymers.

The composition according to the invention may comprise from 0.1 to 40%by weight, preferably from 1 to 30 and in particular from 2 to 20% byweight of surface-active substances, the amount of the alkoxylate (A)and (AQ) not being taken into consideration.

Suitable thickeners are compounds which impart to the formulation amodified flow behavior, i.e. high viscosity at rest and low viscosity inthe agitated state. Examples are polysaccharides, proteins (such ascasein or gelatins), synthetic polymers, or inorganic layered minerals.Such thickeners are commercially available, for example Xanthan Gum(Kelzan®, CP Kelco, USA), Rhodopol® 23 (Rhodia, France) or Veegum® (R.T.Vanderbilt, USA) or Attaclay® (Engelhard Corp., NJ, USA). The thickenercontent in the formulation depends on the efficacy of the thickener. Theskilled worker will choose such a content that the desired viscosity ofthe formulation is obtained. The content will amount to from 0.01 to 10%by weight in most cases.

Bactericides may be added in order to stabilize the composition.Examples of bactericides are those based on dichlorophene and benzylalcohol hemiformal and also isothiazolinone derivatives such asalkylisothiazolinones and benzoisothiazolinones (Acticide® MBS from ThorChemie). Examples of suitable antifreeze agents are ethylene glycol,propylene glycol, urea and glycerol. Examples of antifoams are siliconeemulsions (such as, for example, Silikon® SRE, Wacker, Germany orRhodorsil®, Rhodia, France), long-chain alcohols, fatty acids, salts offatty acids, organofluorine compounds and mixtures of these.

The composition according to the invention can preferably be present inthe form of an agrochemical formulation. Examples of such formulationsand their preparation are:

-   i) Water-soluble concentrates (SL, LS): 10 parts by weight of the    active substances are dissolved using 90 parts by weight of water or    a water-soluble solvent. Alternatively, wetters or other adjuvants    are added. Upon dilution in water, the active substance dissolves.    This gives a composition with an active substance content of 10% by    weight.-   ii) Dispersible concentrates (DC): 20 parts by weight of the active    substances are dissolved in 70 parts by weight of cyclohexanone with    addition of 10 parts by weight of a dispersant, for example    polyvinylpyrrolidone. Upon dilution in water, a dispersion is    obtained. The active substance content amounts to 20% by weight-   iii) Emulsifiable concentrates (EC): 15 parts by weight of the    active substances are dissolved in 75 parts by weight of xylene with    addition of calcium dodecylbenzene-sulfonate and castor oil    ethoxylate (in each case 5 parts by weight). Upon dilution in water,    an emulsion is obtained. The composition has an active substance    content of 15% by weight.-   iv) Emulsions (EW, EO, ES): 25 parts by weight of the active    substances are dissolved in 35 parts by weight of xylene with    addition of calcium dodecylbenzene-sulfonate and castor oil    ethoxylate (in each case 5 parts by weight). Using an emulsifier    (for example Ultra-Turrax), this mixture is placed into 30 parts by    weight of water and made into a homogeneous emulsion. Upon dilution    in water, an emulsion results. The composition has an active    substance content of 25% by weight.-   v) Suspensions (SC, OD, FS): 20 parts by weight of the active    substances are comminuted with addition of 10 parts by weight of    dispersants and wetters and 70 parts by weight of water or an    organic solvent in a stirred-ball mill to give a finely divided    active substance suspension. Upon dilution in water, a stable    suspension of the active substance is obtained. The active substance    content in the composition amounts to 20% by weight.-   vi) Water-dispersible and water-soluble granules (WG, SG): 50 parts    by weight of the active substances are ground finely with addition    of 50 parts by weight of dispersants and wetters and formulated as    water-dispersible or water-soluble granules by means of technical    apparatuses (for example extrusion, spray tower, fluidized bed).    Upon dilution in water, a stable dispersion or solution of the    active substance is obtained. The composition has an active    substance content of 50% by weight.-   vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS):    75 parts by weight of the active substances are ground in a    rotor-stator mill with addition of 25 parts by weight of dispersants    and wetters and also silica gel. Upon dilution in water, a stable    dispersion or solution of the active substance is obtained. The    active substance content of the composition amounts to 75% by    weight.-   viii) Gels (GF): in a ball mill, 20 parts by weight of the active    substances, 10 parts by weight of dispersant, 1 part by weight of    gelling agent and 70 parts by weight of water or an organic solvent    are ground to give a fine suspension. Upon dilution with water, a    stable suspension with an active substance content of 20% by weight    is obtained.-   ix) Dusts (DP, DS): 5 parts by weight of the active substances are    ground finely and mixed intimately with 95 parts by weight of finely    divided kaolin. This gives a dust with an active substance content    of 5% by weight.-   x) Granules (GR, FG, GG, MG): 0.5 part by weight of the active    substances is ground finely and associated with 99.5 parts by weight    of carriers. Conventional methods to this end are extrusion,    spray-drying or the fluidized bed. This gives granules for direct    application with an active substance content of 0.5% by weight.-   xi) ULV solutions (UL): 10 parts by weight of the active substances    are dissolved in 90 parts by weight of an organic solvent, for    example xylene. This gives a composition to be applied directly with    an active substance content of 10% by weight.

In general, the compositions comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the pesticides.

The user will generally use the composition according to the inventionfor use in a premetering device, in a knapsack sprayer, in a spray tankor in a spraying aircraft. Here, the formulation is brought to thedesired use concentration with water and/or buffer, optionally withaddition of further auxiliaries, whereby the ready-to-use spray mixture(known as a tank mix) is obtained. Usually, 50 to 500 liters of theready-to-use spray mixture are applied per hectare of utilizableagricultural area, preferably from 100 to 400 liters. In specificsegments the amounts may also be above (e.g., fruit growing) or below(e.g., aircraft application) these amounts. The active substanceconcentrations in the ready-to-use preparations may be varied withinsubstantial ranges. In general, they are between 0.0001 and 10%,preferably between 0.01 and 1%.

Oils of various types, wetters, drift reduction agents, stickers,spreaders, adjuvants, fertilizers, plant-strengthening products, traceelements, herbicides, bactericides, fungicides and/or pesticides may beadded to the active substances or to the preparations comprising them,optionally also to the tank mix, immediately prior to use. Theseproducts can be admixed to the compositions according to the inventionin the weight ratio 1:100 to 100:1, preferably 1:10 to 10:1. Adjuvantswhich are suitable within this context are in particular:organic-modified polysiloxanes, for example Break Thru S 240®; alcoholalkoxylates, for example Atplus® 245, Atplus® MBA 1303, Plurafac® LF 300and Lutensol® ON 30; EO/PO block polymers, for example Pluronic® RPE2035 and Genapol® B; alcohol ethoxylates, for example Lutensol® XP 80;and sodium dioctyl sulfosuccinate, for example Leophen® RA.

Depending on the nature of the desired effect, the application rates ofthe active substance when used in plant protection are between 0.001 and2.0 kg of active substance per ha, preferably between 0.005 and 2 kg perha, especially preferably between 0.05 and 0.9 kg per ha, in particularbetween 0.1 and 0.75 kg per ha.

The present invention furthermore relates to a method of controllingphytopathogenic fungi and/or undesired vegetation and/or undesiredinsect or mite attack and/or for regulating the growth of plants,wherein the composition according to the invention is allowed to act onthe respective pests, their environment or the plants to be protectedfrom the respective pest, on the soil and/or on undesirable plantsand/or the crop plants and/or their environment.

Examples of suitable crop plants are cereals, for example wheat, rye,barley, triticale, oats or rice; beet, for example sugar or fodder beet;pome fruit, stone fruit and soft fruit, for example apples, pears,plums, peaches, almonds, cherries, strawberries, raspberries, currantsor gooseberries; legumes, for example beans, lentils, peas, lucerne orsoybeans; oil crops, for example oilseed rape, mustard, olives,sunflowers, coconut, cacao, castor beans, oil palm; peanuts or soybeans;cucurbits, for example pumpkins/squash, cucumbers or melons; fibercrops, for example cotton, flax, hemp or jute; citrus fruit, for exampleoranges, lemons, grapefruit or tangerines; vegetable plants, for examplespinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes,potatoes, pumpkin/squash or capsicums; plants of the laurel family, forexample avocados, cinnamon or camphor; energy crops and industrialfeedstock crops, for example maize, soybeans, wheat, oilseed rape, sugarcane or oil palm; maize; tobacco; nuts; coffee; tea; bananas; wine(dessert grapes and grapes for vinification); hops; grass, for exampleturf; sweetleaf (Stevia rebaudania); rubber plants and forest plants,for example flowers, shrubs, deciduous trees and coniferous trees, andpropagation material, for example seeds, and harvested produce of theseplants.

The term crop plants also includes those plants which have been modifiedby breeding, mutagenesis or recombinant methods, including thebiotechnological agricultural products which are on the market or in theprocess of being developed. Genetically modified plants are plants whosegenetic material has been modified in a manner which does not occurunder natural conditions by hybridizing, mutations or naturalrecombination (i.e. recombination of the genetic material). Here, one ormore genes will, as a rule, be integrated into the genetic material ofthe plant in order to improve the plant's properties. Such recombinantmodifications also comprise posttranslational modifications of proteins,oligo- or polypeptides, for example by means of glycosylation or bindingpolymers such as, for example, prenylated, acetylated or farnesylatedresidues or PEG residues.

Examples which may be mentioned are plants which, as the result ofplant-breeding and recombinant measures, have acquired a tolerance forcertain classes of herbicides, such as hydroxyphenylpyruvate dioxygenase(HPPD) inhibitors, acetolactate synthase (ALS) inhibitors such as, forexample, sulfonylureas (EP-A 257 993, U.S. Pat. No. 5,013,659) orimidazolinones (for example U.S. Pat. No. 6,222,100, WO 01/82685, WO00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073),enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors such as,for example, glyphosate (see, for example, WO 92/00377), glutaminesynthetase (GS) inhibitors such as, for example, glufosinate (see, forexample, EP-A 242 236, EP-A 242 246) or oxynil herbicides (see, forexample, U.S. Pat. No. 5,559,024). For example, breeding and mutagenesishave given rise to Clearfield® oilseed rape (BASF SE, Germany), whichfeatures tolerance for imidazolinones, for example imazamox. With theaid of recombinant methods, crop plants such as soybeans, cotton, maize,beet and oilseed rape have been generated which are resistant toglyphosate or glufosinate, and these are available by the brand namesRoundupReady® (glyphosate-resistant, Monsanto, U.S.A.) and Liberty Link®(glufosinate-resistant, Bayer CropScience, Germany).

Also comprised are plants which, with the aid of recombinant measures,produce one or more toxins, for example those from the bacterial strainBacillus. Toxins which are produced by such genetically modified plantscomprise, for example, insecticidal proteins of Bacillus spp., inparticular from B. thuringiensis, such as the endotoxins Cry1Ab, Cry1Ac,Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; orvegetable insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, orVIP3A; insecticidal proteins from nematode-colonizing bacteria, forexample Photorhabdus spp. or Xenorhabdus spp.; toxins from animalorganisms, for example wasp, spider or scorpion toxins; fungal toxins,for example from Streptomycetes; plant lectins, for example from pea orbarley; agglutinins; proteinase inhibitors, for example trypsininhibitors, serine protease inhibitors, patatin, cystatin or papaininhibitors; ribosome-inactivating proteins (RIPs), for example ricin,maize RIP, abrin, luffin, saporin or bryodin; steroid-metabolizingenzymes, for example 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMGCoA-reductase; ion channel blockers, for example inhibitors of sodium orcalcium channels; juvenile hormone esterase; receptors for the diuretichormone (helicokinin receptors); stilbene synthase, bibenzyl synthase,chitinases and glucanases. These toxins can also be produced, in theplants, in the form of pretoxins, hybrid proteins, truncated orotherwise modified proteins. Hybrid proteins are distinguished by anovel combination of different protein domains (see, for example, WO2002/015701). Further examples of such toxins or genetically modifiedplants which produce these toxins are disclosed in EP-A 374 753, WO93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO03/52073. The methods for generating these genetically modified plantsare known to the skilled worker and explained, for example, in theabovementioned publications. A large number of the abovementioned toxinsimpart to the plants which produce them a tolerance for pests from alltaxonomic classes of the arthropods, in particular beetles (Coeleropta),dipterans (Diptera) and lepidopterans (Lepidoptera) and nematodes(Nematoda). Genetically modified plants which produce one or more geneswhich code for insecticidal toxins are described for example in theabovementioned publications and are in some cases commercially availablesuch as, for example, YieldGard® (maize varieties which produce thetoxin Cry1Ab), YieldGard® Plus (maize varieties which produce the toxinsCry1Ab and Cry3Bb1), Starlink® (maize varieties which produce the toxinCry9c), Herculex® RW (maize varieties which produce the toxins Cry34Ab1,Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT]);NuCOTN® 33B (cotton varieties which produce the toxin Cry1Ac), Bollgard®I (cotton varieties which produce the toxin Cry1Ac), Bollgard® II(cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT®(cotton varieties which produce a VIP toxin); NewLeaf® (potato varietieswhich produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®,BiteGard®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 fromSyngenta Seeds SAS, France, (maize varieties which produce the toxinCry1Ab and the PAT enzyme), MIR604 from Syngenta Seeds SAS, France(maize varieties which produce a modified version of the toxin Cry3A,see in this context WO 03/018810), MON 863 from Monsanto Europe S.A.,Belgium (maize varieties which produce the toxin Cry3Bb1), IPC 531 fromMonsanto Europe S.A., Belgium (cotton varieties which produce a modifiedversion of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation,Belgium (maize varieties which produce the toxin Cry1F and the PATenzyme).

Also comprised are plants which, with the aid of recombinant measures,produce one or more proteins which bring about an increased resistanceto, or ability to withstand, bacterial, viral or fungal pathogens suchas, for example, so-called pathogenesis-related proteins (PR proteins,see EP-A 0 392 225), resistance proteins (for example potato varietieswhich produce two resistance genes against Phytophthora infestans fromthe Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (forexample potato varieties which, as the result of the production of thisprotein, are resistant to bacteria such as Erwinia amylvora).

Also comprised are plants whose productivity has been improved with theaid of recombinant methods, for example by increasing the yieldpotential (for example biomass, grain yield, starch content, oil contentor protein content), the tolerance for drought, salt or other limitingenvironmental factors, or the resistance to pests and fungal, bacterialand viral pathogens.

Also comprised are plants whose constituents, in particular forimproving human or animal nutrition, have been modified with the aid ofrecombinant methods, for example by oil plants producinghealth-promoting long-chain omega-3-fatty acids or monounsaturatedomega-9-fatty acids (for example Nexera® oilseed rape, DOW AgroSciences, Canada).

The present invention also relates to seed (such as seeds or other plantpropagation materials) comprising the composition according to theinvention. Plant propagation materials can be treated preventively withthe composition according to the invention at the point of or evenbefore sowing or at the point of or even before transplanting. For thetreatment of seed, one will generally use water-soluble concentrates(LS), suspensions (FS), dusts (DS), water-dispersible and water-solublepowders (WS, SS), emulsions (ES), emulsifiable concentrates (EC) andgels (GF). These compositions can be applied to the propagationmaterials, in particular seed, in undiluted form or, preferably, indiluted form. Here, the composition in question can be diluted 2- to10-fold, so that from 0.01 to 60% by weight, preferably from 0.1 to 40%by weight, of active substance is present in the compositions used forthe seed dressing. The application may be effected before or duringsowing. The treatment of plant propagation material, in particular thetreatment of seed, is known to the skilled worker and carried out bydusting, coating, pelleting, dipping or soaking the plant propagationmaterial, the treatment preferably being carried out by pelleting,coating and dusting or by in-furrow treatment so that, for example,untimely early germination of the seed is prevented. It is preferred touse suspensions for the treatment of seed. Usually, such compositionscomprise from 1 to 800 g/l of active substance, from 1 to 200 g/l ofsurfactants, from 0 to 200 g/l of antifreeze agents, from 0 to 400 g/lof binders, from 0 to 200 g/l of colorants and solvent, preferablywater.

The present invention furthermore relates to an alkoxylate, wherein thealkoxylate is an amine alkoxylate (A)

or a quaternized derivative (AQ)

of the amine alkoxylate (A), where

-   R¹, R², and R⁵ independently of one another are ethylene, propylene,    butylene or a mixture of these,-   R³ is an H, —OH, —OR⁴, —[R⁵—O]_(p)—R⁶, C₁-C₆-alkyl or an oxygen    anion,-   R⁴ is a C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl,-   R⁶ is an H, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —SO₃R^(a),    —P(O)OR^(b)OR^(c), —CH₂CO₂R^(d), or —C(O)R^(e),-   R^(a) and R^(d) independently of one another are an H, inorganic or    organic cations,-   R^(b) and R^(c) independently of one another are an H, inorganic or    organic cations, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl,-   R^(e) is C₁-C₂₂-alkyl, C₂-C₂₂-alkenyl, C₂-C₂₂-alkynyl, C₆-C₂₂-aryl    or C₇-C₂₂-alkylaryl,-   n, m and p independently of one another have a value of from 1 to    30,-   A⁻ is an agriculturally acceptable anion, or, if R³ is an oxygen    anion, A⁻ is absent. Preferred parameters are as described above.

In one embodiment the alkoxylate is a quaternized derivative (AQ) of theamine alkoxylate (A). In a preferred embodiment, the alkoxylate is anamine alkoxylate (A).

In a further preferred embodiment, the alkoxylate is a quaternizedderivative (AQ) of the amine alkoxylate (A). Here, A⁻ is preferably ahalide (such as chloride or bromide), phosphate, sulfate or an anionicpesticide. A⁻ is especially preferably an anionic pesticide, such asglyphosate anion or glufosinate anion.

The present invention furthermore relates to processes for thepreparation of the amine alkoxylate (A) or a quaternized derivative (AQ)of the amine alkoxylate (A), comprising the alkoxylation of2-propylheptylamine with ethylene oxide, propylene oxide, butylene oxideor a mixture of these. The preparation of 2-propylheptylamine isgenerally known, for example by reacting ammonia with 2-propylheptanolas described in U.S. Pat. No. 5,808,158.

The alkoxylation can be catalyzed by strong bases, such as alkali metalhydroxides and alkaline earth metal hydroxides, Brönsted acids or Lewisacids, such as AlCl₃, BF₃. Catalysts such as hydrotalcite or DMC may beused for alcohol alkoxylates with a narrow distribution. Thealkoxylation is preferably carried out at temperatures in the range ofapproximately 80 to 250° C., preferably approximately 100 to 220° C. Thepressure is preferably between ambient pressure and 600 bar. If desired,the alkylene oxide may comprise an admixture of inert gas, for exampleof approximately 5 to 60%.

The quaternized derivative (AQ) of the amine alkoxylate (A) can beprepared in a further reaction step by quaternizing the amine alkoxylate(A). To introduce the radical R³ into the amine alkoxylate (A), thelatter may be reacted for example with an alkylation reagent such asmethyl chloride, dimethyl sulfate or butyl chloride. To introduce theone oxygen anion into the amine alkoxylate (A), the latter may beoxidized, for example by reacting the amino group with hydrogenperoxide, peracids (such as meta-chloroperbenzoic acid or peraceticacid) or peroxomonosulfuric acid.

The quaternized derivatives (AQ) where R³═H can be prepared by simpleprotonation of starting compounds of the structure (A). The quaternizedderivatives (AQ) where R³═OH can be prepared by simple protonation ofstarting compounds (AQ) where R³=oxygen anion. Acids which are suitablefor the protonation are organic acids (for example C₁- to C₂₀-carboxylicacids, in particular benzoic acid) or inorganic acids (for examplehydrochloric acid, phosphoric acid or sulfuric acid). Others which arelikewise suitable are H-acidic pesticides such as, for example,glyphosate-acid or glyphosate-monosalts. The protonation can be carriedout in a separate synthesis, so that the quaternized derivative (AQ) canbe isolated. It is also possible to carry out the protonation by mixingthe starting compounds with one or more acids in the composition or inthe spray mixture.

The present invention also relates to the use of the amine alkoxylate(A) or of a quaternized derivative (AQ) of the amine alkoxylate (A) asdescribed above as auxiliary in pesticide-comprising spray mixtures. Theauxiliary is preferably an activity-enhancing auxiliary. Suchactivity-enhancing auxiliaries are also referred to as adjuvants. Theyenhance or accelerate the activity of pesticides in comparison with theactivity of the pesticide in the absence of the adjuvant.

The advantages of the invention are high stability of the formulationand of the spray mixture, little wind-caused drift in the case of sprayapplications, good adhesion of the formulation on the surface of thetreated plants, increased solubility of the pesticides in theformulation, increased permeation of the pesticides into the plant and,as a result, more rapid and enhanced activity. An important advantage isthe low toxicity of the novel alkoxylates, in particular the low aquatictoxicity. Another advantage is the low harmful effect against cropplants, i.e., low phytotoxic effects. A further advantage is the simplehandling of these alkoxides since, for example, no gelling takes placeupon their incorporation into formulations.

The examples which follow illustrate the invention without imposing anylimitation.

EXAMPLES Example 1 Synthesis of 2-propylheptylamine (2-PHamine)

2-Propylheptanol (commercially available from BASF SE or Evonik) and analcohol amination catalyst (described in EP 696 572 A1; 8% by weightbased on 2-propylheptanol) were introduced in the autoclave, and thesystem was flushed with nitrogen and hydrogen. Then ammonia was injectedin a molar ratio of ammonia to alcohol of 17:1 and the mixture washeated with stirring. After a reaction time of ten hours at 210° C. andan H₂ pressure of 240 bar, the 2-propylheptylamine was filtered off andfreed from water on a rotary evaporator.

Example 2 Alkoxylation of 2-propylheptylamine A) Preparation of2-PHamine-7 EO

First of all 628 g (4 mol) of 2-propylheptylamine from Example 1 wereadmixed with 19.6 g of water. Then, after flushing with nitrogen, at100° C., 352 g (8 mol) of ethylene oxide (EO) were metered in.Subsequently, at 80° C., this batch was dewatered under reducedpressure. This gave a yield of 988 g (=99% of theory) with an OH numberof 468 mg KOH/g (458 mg KOH/g theory) and an amine number of 229 mgKOH/g (229 mg KOH/g theory).

In a second step, 269.5 g (1.1 mol) of this precursor product wereadmixed with 2.0 g of 50% strength KOH, and dewatering took place at 90°C. under reduced pressure. After flushing with nitrogen, at 120° C., 242g (=5.5 mol) of ethylene oxide were metered in. The product was adjustedto a pH (5% in water) of 9.9 with a few drops of acetic acid. This gavea yield of 512 g (100% of theory) of a yellowish liquid of low viscosity(OH number: 279.1 mg KOH/g (241 mg KOH/g theory); amine number: 120 mgKOH/g (121 mg KOH/g theory), water content<0.5% by weight).

B) Preparation of 2-PHamine-10 EO

First of all, 1280 g (8.15 mol) of 2-propylheptylamine from Example 1were admixed with 40 g of water. Then, after flushing with nitrogen, at100° C., 717 g (16.3 mol) of ethylene oxide were metered in (2 bar, 16h). Subsequently, at 90° C., remaining traces of ethylene oxide wereremoved under reduced pressure. This gave a quantitative yield with anamine number of 229 mg KOH/g.

In the second step, 821.5 g (3.35 mol) of this precursor product wereadmixed with 8.0 g of 50% strength KOH and dewatering was carried out at90° C. under reduced pressure. After flushing with nitrogen, at 120° C.,1179 g (=26.8 mol) of ethylene oxide were metered in (1.5 bar, 12 h).This gave a quantitative yield of a yellowish liquid of low viscosity.

C) to F) Preparation of 2-PHamine-5 EO, 2-PHamine-8.5 EO, 2-PHamine-15EO, 2-PHamine-20 EO

The ethoxylation of 2-propylheptylamine from Example 1 was carried outin accordance with Examples 2A and 2B. In this way it was possible inquantitative yield to synthesize 2-PHamine-5 EO, 2-PHamine-8.5 EO,2-PHamine-15 EO and 2-PHamine-20 EO. Here, the codes “−5 EO”, “−8.5 EO”,etc., indicate the molar excess of ethylene oxide relative to2-propylheptylamine.

G) Preparation of 2-PHamine-ethoxylate-propoxylate

General preparation instructions: 2-propylheptylamine (1 mol eq.; fromExample 1) was admixed in the reactor with water (2% by weight, based onthe total batch). Then, after flushing with nitrogen and adjustment ofthe pressure to 1.5 bar, at 100° C.-130° C., ethylene oxide (2 mol eq.)was metered in. This was followed by dewatering at 80° C. under reducedpressure. The yield is determined, and also the OH number and aminenumber, in order to determine the quality of the precursor product.

In the second step, this precursor product (1 mol eq.) was admixed with50% strength KOH (0.2% by weight, based on the total batch) anddewatering was carried out at 90° C. under reduced pressure. Afterflushing with nitrogen, the pressure is adjusted to 1.5 bar and, at 120°C.-140° C., alkylene oxide (x mol eq. of ethylene oxide or propyleneoxide or a mixture of propylene oxide or ethylene oxide) is metered in.The reaction mixture was stirred at this temperature until the pressurewas constant.

Either the product was discharged and adjusted with glacial acetic acidto a pH of 9.9 (5% in water), or at the same temperature (120-140° C.)propylene oxide (y mol eq.) is metered in. The reaction mixture isstirred at this temperature until the pressure is constant. The productis isolated and adjusted with glacial acetic acid to a pH of 9.9 (5% inwater).

The alkoxylation of 2-propylheptylamine to give 2-PHamine-5 EO-15 PO wascarried out in accordance with the general preparation instructions. Inthe first step, reaction took place with a 2-molar excess of ethyleneoxide, and in the second step the remaining ethylene oxide and propyleneoxide were added. This gave 2-PHamine-5 EO-15 PO in quantitative yield.

H to Q) Preparation of 2-PHamine-propoxylate-ethoxylate

General preparation instructions: 2-propylheptylamine (1 mol eq.) wasadmixed in the reactor with water (2% by weight, based on the totalbatch). Then, after flushing with nitrogen and adjustment of thepressure to 1.5 bar, at 100° C.-130° C., propylene oxide (2 mol eq.) wasmetered in. This was followed by dewatering at 80° C. under reducedpressure. The yield was determined, and also the OH number and aminenumber, in order to determine the quality of the precursor product.

In the second step, this precursor product (1 mol eq.) was admixed with50% strength KOH (0.2% by weight, based on the total batch) anddewatering was carried out at 90° C. under reduced pressure. Afterflushing with nitrogen, the pressure is adjusted to 1.5 bar and, at 120°C.-140° C., alkylene oxide (x mol eq. of ethylene oxide or propyleneoxide or a mixture of propylene oxide or ethylene oxide) is metered in.The reaction mixture is stirred at this temperature until the pressureis constant.

Either the product was discharged and adjusted with glacial acetic acidto a pH of 9.9 (5% in water), or at the same temperature (120-140° C.)propylene oxide (y mol eq.) was metered in. The reaction mixture wasstirred at this temperature until the pressure was constant. The productwas isolated and adjusted with glacial acetic acid to a pH of 9.9 (5% inwater).

In accordance with these instructions, the following alkoxylates wereprepared, each with a quantitative yield:

I) 2-PHamine-2 PO-5 EO J) 2-PHamine-2 PO-10 EO K) 2-PHamine-2 PO-15 EOL) 2-PHamine-4 PO-5 EO M) 2-PHamine-4 PO-10 EO N) 2-PHamine-4 PO-15 EOO) 2-PHamine-6 PO-5 EO P) 2-PHamine-6 PO-10 EO Q) 2-PHamine-6 PO-15 EOExample 3 Glyphosate SL Formulation Against Brachiarea multica

In a field trial, seven experimental areas of in each case six squaremeters were subjected to treatment against the weed Brachiarea multica,in each case in two replications (i.e. two plots of in each case 3 m²).To this end, in each case 1.01 of spray solution (see table 1) wassprayed per plot using a manual sprayer. 1.01 of the spray solutioncontained 7.5 ml of an aqueous formulation of dissolvedglyphosate-isopropylammonium salt. To prepare this formulation, 100 mlof amine alkoxylate of example 2 were previously made up to 1.01 with46% strength glyphosate-isopropylammonium salt solution. Two, five andseven days after the application, the destruction of the weed wasestimated visually in percent. Rain fell repeatedly in the days betweenapplication and assessment.

For comparison purposes, a glyphosate formulation as above, but withoutamine alkoxylate, was prepared, and a commercial glyphosate formulation(Roundup®, Monsanto) which comprised 41.5% by weight ofglyphosate-isopropylammonium salt and 15.5% by weight of ethoxylatedtallow fatty amine with approximately 15 mol of ethylene oxide per aminegroup (“tallow fatty amine—15 EO”) was also used.

TABLE 1 Proportion [%] of weed destroyed Amine alkoxylate 2 days 5 days7 days — ^(a)) 15 35 55 Tallow fatty amine--15 EO ^(a)) 40 70 752-Ethylhexylamine-7 EO ^(a)) 25 60 77.5 Isotridecylamine-9 EO ^(a)) 2040 62 2-PHamine-7 EO (from Example 2) 40 87.5 90 ^(a)) Comparativeexperiment, not inventive.

The data in table 1 demonstrated that the 2-propylheptylamine ethoxylateaccording to the invention (“2-PHamine-7 EO”) enhances and acceleratesthe activity of glyphosate. Also, the formulation was rainfast. Attemperatures of from 5 to +55° C., the formulation was storage-stablefor at least two weeks.

Upon addition of 2-PHamine-7 EO at 20° C. to the glyphosate solution,there was, advantageously, no gelling observed, as was usually the casewhen tallow fatty amine-1-15 EO was added.

Example 4 Water Toxicity

-   -   2-PHamine-7 EO (from Example 2): EC50 60 mg/l (48 h) on Daphnia        magna, determined according to OECD Guideline 202 part 1.    -   2-PHamine-10 EO (from Example 2): fish toxicity LC50>100 mg/l        (96 h), Brachydanio rerio, determined according to OECD 203; ISO        7346; 84/449/EEC, C.1; EC50 (72 h)>100 mg/l, algae, determined        according to OECD Guideline 201.    -   Lutensol® FA15 T (tallow fatty amine ethoxylate with 15 EO):        EC50 2.6 mg/l (48 h) on Daphnia magna, determined according to        OECD Guideline 202 part 1; fish toxicity LC50 1-10 mg/l (96 h),        Leuciscus idus (safety data sheet of Mar. 8, 2006 from BASF SE).    -   Lutensol® FA 12 (oleylamine ethoxylate with 12 EO): EC50 0.1-1        mg/l (48 h) on Daphnia magna, fish toxicity LC50 1-10 mg/l (96        h), Leuciscus idus (safety data sheet of Aug. 18, 2006 from BASF        SE).

Example 5 Glyphosate SL Formulation on Oilseed Rape

For the greenhouse tests, winter oilseed rape (cultivar Remy) was sownor potted in loamy sandy soil to a depth of 1-2 cm. When the plants hadreached a growth height of 10 to 25 cm (i.e., around 10 to 21 days aftersowing), the spray mixtures were applied to the plants in a sprayingcabin.

A concentrated formulation comprising glyphosate isopropylammonium insolution in water and amine alkoxylate from Example 2 was diluted withdeionized water and applied at a water application rate of 375 l/ha (140g of glyphosate/ha and 300 g of amine alkoxylate/ha). The temperaturesin the experimental period, which lasted for 3 to 4 weeks, were between18-35° C. During this time, the experimental plants received optimumwatering, with nutrients being supplied via the water used for watering.

The herbicidal activity was evaluated by awarding scores to the treatedplants in comparison to the untreated control plants (Table 2). Theevaluation scale ranges from 0% to 100% activity. 100% activity meansthe complete death at least of those parts of the plant that are aboveground. Conversely, 0% activity means that there were no differencesbetween treated and untreated plants. The results in Table 2 demonstratethe increased activity of the active substance as a result of additionof the amine alkoxylate.

TABLE 2 Activity [%] Activity [%] Amine alkoxylate after 14 days after21 days — ^(a)) 51 69 2-PHamine-5 EO 59 74 2-PHamine-7 EO 75 862-PHamine-10 EO 74 86 2-PHamine-15 EO 63 74 2-PHamine-20 EO 63 742-PHamine-5 EO-15 PO 63 74 N-Methyl-2-PHamine-7 EO ^(a), b)) 56 65 ^(a))Comparative experiment, not inventive, ^(b)) Prepared in analogy to WO2009/004044, by addition of methylamine to the corresponding enone,which was then ethoxylated in the same way as in Example 2A. The neutralN-methylamine (not quaternized) obtained in this way had an amine numberof 117.8 mg KOH/g).

Example 6 Glyphosate SL Formulation on Wheat, Soybean or Maize

The experiments were carried out as in Example 5, on winter wheat(cultivar Cubus), soybean (cultivar Oxford), and maize (cultivarAmadeo). The application rate was 280 g of glyphosate/ha and 300 g ofamine alkoxylate/ha. The results in Table 3 demonstrate the increasedactivity of the active substance as a result of addition of the aminealkoxylate.

TABLE 3 Activity [%] after 21 days Amine alkoxylate Winter wheat SoybeanMaize — ^(a)) 73 38 54 2-PHamine-8.5 EO 96 93 89 2-Ethylhexylamine-7 EO^(a)) 84 51 71 ^(a)) Comparative experiment, not inventive.

Example 7 Glyphosate SL Formulation on Oilseed Rape

The experiments were carried out as in Example 5, on winter oilseed rape(cultivar Remy). The application rate was 140 g of glyphosate/ha and 300g of amine alkoxylate/ha. The results in Table 4 demonstrate theincreased activity of the active substance as a result of addition ofthe amine alkoxylate.

TABLE 4 Activity [%] Activity [%] Amine alkoxylate after 14 days after21 days — ^(a)) 51 69 2-PHamine-2 PO-5 EO 94 97 2-PHamine-2 PO-10 EO 9291 2-PHamine-2 PO-15 EO 97 98 2-PHamine-4 PO-5 EO 86 86 2-PHamine-4PO-10 EO 92 91 2-PHamine-4 PO-15 EO 94 93 2-PHamine-6 PO-5 EO 83 802-PHamine-6 PO-10 EO 86 84 2-PHamine-6 PO-15 EO 91 86 ^(a)) Comparativeexperiment, not inventive.

Example 8 Imazamox SL Formulation on ambrosia and chenopodium

The experiments were carried out as in Example 5, on Ambrosiaartemisiifolia (AMBEL) and Chenopodium album (CHEAL) and scored after 14days. The spray mixture was prepared starting from an aqueous SLformulation containing 120 g/l imazamox ammonium salt and 1.2-propyleneglycol. The application rate was 10 g of imazamox/ha and 400 g of aminealkoxylate/ha. The results are summarized in Table 5. For comparison, atallow fatty amine ethoxylate with 12 ethylene oxide units was used(liquid, approximately 100% content, molar mass approximately 730 g/mol(calculated from OH number), available commercially as Lutensol® FA12Kfrom BASF SE).

TABLE 5 Activity [%] Activity [%] Amine alkoxylate AMBEL CHEALLutensol ® FA12K ^(a)) 80 90 2-PHamine-5 EO 80 93 2-PHamine-7 EO 80 932-PHamine-10 EO 83 90 2-PHamine-15 EO 80 93 2-PHamine-20 EO 85 93 ^(a))Comparative experiment, not inventive.

Example 9 Imazaquin, Chlormequat Chloride and Choline Chloride SLFormulation for Growth Regulation in Wheat

The experiments were carried out as in Example 5, on wheat. The heightof the stalks was measured 7, 14 and 21 days after application. Thespray mixture was prepared starting from an aqueous SL formulationcontaining 0.8 g/l imazaquin, 368 g/l chlormequat chloride, 28 g/lcholine chloride, and 80 g/l amine alkoxylate from Example 2C(2-PHamine-10 EO). The application rate was 1500 g/ha, 1000 g/ha or 500g/ha of chlormequat chloride. The results are summarized in Table 6.

TABLE 6 Height of the wheat stalks [cm] 7, 14 and 21 days afterapplication Application rate of chlormequat chloride 7 days 14 days 21days — ^(a)) 30.1 32.5 39.3 1500 g/ha 25.1 25.1 26.4 1000 g/ha 25.8 27.127.0  500 g/ha 22.3 27.4 26.9 ^(a)) Untreated wheat, comparativeexperiment, not inventive.

Example 10 Rain Resistance

Four maize plants and four winter wheat plants were each treated with280 g/ha of glyphosate isopropylammonium salt and 300 g/ha of aminealkoxylate. After 1.5 or 3 h following this treatment, the plants wereirrigated for 20 minutes with 1001 of water, at a pressure of 3.33 barand a rate of 2.8 m/s. The plants were then placed in a greenhouse andrated as in Example 5 after 14 and 21 days. For comparison, Genamine® T150 was used (C_(16/18)-amine ethoxylate with 15 EO units, availablecommercially from Clariant).

Table 7 shows that the irrigation detaches the glyphosate less stronglyfrom the plant, and so the activity remains high even after irrigation.

TABLE 7 Activity [%] after 21 days No Irrigation 3 h Amine alkoxylateirrigation after application No application ^(a)) Maize 0 — Genamine ® T150 ^(a)) Maize 98 53 2-PHamine-2 10 EO Maize 98 71 No application ^(a))Wheat 0 — Genamine ® T 150 ^(a)) Wheat 100 94 2-PHamine-2 10 EO Wheat100 97 ^(a)) Comparative experiment, not inventive.

Example 11 Water-Soluble Granules SG

Glyphosate monoammonium salt (80.75 g) was mixed thoroughly with sodiumsulfite (0.5 g) in a coffee grinder. The mixture was subsequently pastedup with a solution of 18.7 g of 2-PHamine-15 EO (from Example 2) and 4 gof water and extruded (benchtop, 0.8 mm perforated plate). The extrudatewas subsequently dried and comminuted in order to give an extremelyhomogeneous granule size (average length approximately 1 mm). Thewater-soluble glyphosate granules (SG) obtained in this way werephysically and chemically stable. From these granules it was possible,by dissolving them in water, to prepare spray mixtures (e.g., 2%strength) in a simple way, which were of high quality and stability.

1-14. (canceled) 15: A herbicide comprising a glyphosate formulationcontaining as a surfactant an alkylamine of Formula

wherein R₁ is a 2-propylheptyl group; and wherein n is 1 to 15 and m is1 to
 15. 16: The herbicide of claim 15, wherein said herbicidecomprises: (a) glyphosate; (b) water; (c) said surfactant; and (d) abuffer; wherein said glyphosate is present as isopropyl-amine salt.